Azetidin-3-ones from (S)-α-Amino Acids and Their Reactions with Nucleophiles: Preparation of some azetidine-containing amino-alcohol and amino-acid derivatives

doi:10.1002/HLCA.19950780516

Paper

Azetidin-3-ones from (S)-α-Amino Acids and Their Reactions with Nucleophiles: Preparation of some azetidine-containing amino-alcohol and amino-acid derivatives

Published Aug 9, 1995 · J. Podlech, D. Seebach

Helvetica Chimica Acta

Q2 SJR score

38

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0

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Abstract

The reactions of azetidin-3-ones 6–10, readily available from the amino acids L-alanine, L-phenylalanine, L-valine, L-lysine, and L-aspartic acid, via the corresponding diazo ketones, with nucleophilic reagents such as complex hydrides, Grignard compounds, an ester enolate, and a Wittig ylide give the expected products 11–19 in good yields and mostly in high diastereoselectivities. New amino-alcohol, γ-amino- and γ-amino-β-hydroxy-carboxylic-acid derivatives of known configurations are thus available.

Study Snapshot

Azetidin-3-ones from amino acids can be converted into new amino-alcohol, -amino- and -amino--hydroxy-carboxylic-acid derivatives with high diastereoselectivities.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Azetidin-3-ones from (S)-α-Amino Acids and Their Reactions with Nucleophiles: Preparation of some azetidine-containing amino-alcohol and amino-acid derivatives

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References

7-azetidinylquinolones as antibacterial agents. 2. Synthesis and biological activity of 7-(2,3-disubstituted-1-azetidinyl)-4-oxoquinoline- and -1,8-naphthyridine-3-carboxylic acids. Properties and structure-activity relationships of quinolones with an azetidine moiety.

Azetidinylquinolones with a combination of a cyclopropyl or substituted phenyl group at N-1 and a trans-3-amino-2-methyl-1-azetidinyl group at C-7 show the best overall antibacterial, pharmaco

Structure and Reactivity of Five‐ and Six‐Ring N, N‐, N, O‐, and O, O‐acetals: A lesson in allylic 1, 3‐strain (A1, 3 strain)

The A',3 strain effect of amide moieties plays a significant role in stereoselective syntheses, leading to structural differences and steric biases in heterocycles.

Rhodium-catalyzed Carbon-Carbon Bond Formation

Rhodium-catalyzed reactions enable efficient carbon-carbon bond formation under neutral conditions, with unique properties in silylformylation and cyclocarbonylation.

Synthesis of 1-alkyl-3-hydroxy-2-phenylazetidines

(R ,S )-1-alkyl-3-hydroxy-2-phenylazetidines (1) were synthesized by the reaction of (R ,S )-2-(1-bromobenzyl)oxirane (2a) with aliphatic primary amine

The Chemistry of β-lactams

Beta-lactams are essential antibiotics, with their biosynthesis, structure-activity relationships, and mode of action influencing their effectiveness against various pathogens.

Citations

Cleavage of Carbon-Carbon σ-Bonds of Four-Membered Rings.

Cleavage of carbon-carbon bonds in four-membered rings offers unique synthetic potentials for complex natural products and structures, offering efficient methods to construct organic skeletons.

Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4 + 2) Cyclization.

Nickel-catalyzed (4 + 2) cycloaddition of alkynes and azetidinones toward piperidinones allows for the enantioselective synthesis of naturally occurring indolizidine alkaloids, such as (+)-septicine, (+

Six-Step Syntheses of (-)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N-Z-O-TBDPS-l-serinal.

This study presents a highly stereoselective six-step syntheses of (-)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannonojirimycin (manno-DNJ) from N-Cbz-O-TBDP

An in Situ Approach to Nickel-Catalyzed Cycloaddition of Alkynes and 3-Azetidinones.

This study developed an efficient and convenient method for nickel-catalyzed cycloaddition of alkynes and 3-azetidinones, yielding useful 3-dehydropiperidinones and 3-dehydropyranone products.

1,5-Rhodium shift in rearrangement of N-arenesulfonylazetidin-3-ols into benzosultams.

This reaction enables the synthesis of enantiopure benzosultams from -amino acids, with potential applications in pharmaceutical and biotechnology industries.

Azetidin-3-ones from (S)-α-Amino Acids and Their Reactions with Nucleophiles: Preparation of some azetidine-containing amino-alcohol and amino-acid derivatives

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References

7-azetidinylquinolones as antibacterial agents. 2. Synthesis and biological activity of 7-(2,3-disubstituted-1-azetidinyl)-4-oxoquinoline- and -1,8-naphthyridine-3-carboxylic acids. Properties and structure-activity relationships of quinolones with an azetidine moiety.

Azetidinylquinolones with a combination of a cyclopropyl or substituted phenyl group at N-1 and a trans-3-amino-2-methyl-1-azetidinyl group at C-7 show the best overall antibacterial, pharmaco

Structure and Reactivity of Five‐ and Six‐Ring N, N‐, N, O‐, and O, O‐acetals: A lesson in allylic 1, 3‐strain (A1, 3 strain)

The A',3 strain effect of amide moieties plays a significant role in stereoselective syntheses, leading to structural differences and steric biases in heterocycles.

Rhodium-catalyzed Carbon-Carbon Bond Formation

Rhodium-catalyzed reactions enable efficient carbon-carbon bond formation under neutral conditions, with unique properties in silylformylation and cyclocarbonylation.

Synthesis of 1-alkyl-3-hydroxy-2-phenylazetidines

(R *,S * )-1-alkyl-3-hydroxy-2-phenylazetidines (1) were synthesized by the reaction of (R *,S * )-2-(1-bromobenzyl)oxirane (2a) with aliphatic primary amine

The Chemistry of β-lactams

Beta-lactams are essential antibiotics, with their biosynthesis, structure-activity relationships, and mode of action influencing their effectiveness against various pathogens.

Citations

Cleavage of Carbon-Carbon σ-Bonds of Four-Membered Rings.

Cleavage of carbon-carbon bonds in four-membered rings offers unique synthetic potentials for complex natural products and structures, offering efficient methods to construct organic skeletons.

Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4 + 2) Cyclization.

Nickel-catalyzed (4 + 2) cycloaddition of alkynes and azetidinones toward piperidinones allows for the enantioselective synthesis of naturally occurring indolizidine alkaloids, such as (+)-septicine, (+

Six-Step Syntheses of (-)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N-Z-O-TBDPS-l-serinal.

This study presents a highly stereoselective six-step syntheses of (-)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannonojirimycin (manno-DNJ) from N-Cbz-O-TBDP

An in Situ Approach to Nickel-Catalyzed Cycloaddition of Alkynes and 3-Azetidinones.

This study developed an efficient and convenient method for nickel-catalyzed cycloaddition of alkynes and 3-azetidinones, yielding useful 3-dehydropiperidinones and 3-dehydropyranone products.

1,5-Rhodium shift in rearrangement of N-arenesulfonylazetidin-3-ols into benzosultams.

This reaction enables the synthesis of enantiopure benzosultams from -amino acids, with potential applications in pharmaceutical and biotechnology industries.

(R ,S )-1-alkyl-3-hydroxy-2-phenylazetidines (1) were synthesized by the reaction of (R ,S )-2-(1-bromobenzyl)oxirane (2a) with aliphatic primary amine